1-Bromo-2-naphthol → HCID 50992704, 화합물

HRID 1189600

반응식

HRID 1189600 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.Br[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[OH:22].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)C.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[OH:22]

참가 물질

8

반응물 4

HCID 113161-Bromo-2-naphtholHCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 27343542-Fluorophenylboronic acid

생성물 1

HCID 50992704HCID 50992704, 화합물수율 69%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 702Ethanol용매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

Into a 200 mL three-neck flask were placed 1.4 g (10 mmol) of 2-fluorobenzeneboronic acid, 2.2 g (10 mmol) of 1-bromo-2-naphthol, 153 mg (0.5 mmol) of tri(o-tolyl)phosphine, 25 mL of toluene, 25 mL of ethanol, and 5.0 mL of a 2M aqueous solution of potassium carbonate. This mixture was degassed under reduced pressure, and the air in the system was replaced with nitrogen. This mixture was stirred at 80° C., 23 mg (0.1 mmol) of palladium(II) acetate was added thereto, and the mixture was refluxed at about 100° C. for 6.5 hours. After the reflux, this mixture was washed with water, and the aqueous layer was subjected to extraction with ethyl acetate. The obtained solution of the extract and the organic layer were combined and washed with saturated brine. The obtained organic layer was dried with magnesium sulfate. This mixture was gravity-filtered, and the obtained filtrate was concentrated to give a brown oily substance. This oily substance was purified by silica gel column chromatography (developing solvent: toluene), so that 1.6 g of a brown oily substance of the object of the synthesis was obtained in 69% yield. The reaction scheme of Step 1 is illustrated in (E1-1).

후처리

  1. customInto a 200 mL three-neck flask were placed
  2. customThis mixture was degassed under reduced pressure
  3. temperaturethe mixture was refluxed at about 100° C. for 6.5 hours
  4. washAfter the reflux, this mixture was washed with water
  5. extractionthe aqueous layer was subjected to extraction with ethyl acetate
  6. extractionThe obtained solution of the extract
  7. washwashed with saturated brine
  8. dry with materialThe obtained organic layer was dried with magnesium sulfate
  9. filtrationThis mixture was gravity-filtered
  10. concentrationthe obtained filtrate was concentrated
  11. customto give a brown oily substance
  12. customThis oily substance was purified by silica gel column chromatography (developing solvent: toluene), so that 1.6 g of a brown oily substance of the object of the synthesis
  13. customwas obtained in 69% yield
  14. customThe reaction scheme of Step 1

출처 및 근거

ORD 기록
ord-a68a8049c63445bcacc3529f009e74f0
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674117B2

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